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Letters in Drug Design & Discovery

Author(s): Hummera Rafique*, Aamer Saeed, Ehsan Ullah Mughal, Muhammad Naveed Zafar, Amara Mumtaz, Naghmana Kausar and Kiran Hina

DOI: 10.2174/1570180815666180502114402

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Total Synthesis and Antibacterial Screening of (±)-6,8-Dihydroxy-3- undecyl-3,4-dihydroisochromen-1-one: A Structural Analogue of Metabolites from Ononis natrix

Page: [245 - 248] Pages: 4

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Abstract

Background: (±)-6,8-Dihydroxy-3-undecyl-3,4-dihydroisochromen-1-one is one of the structural analog of several substituted undecylisocoumarins isolated from Ononis natrix (Fabaceae), has been successfully synthesized by direct condensation of homopthalic acid (1) with undecanoyl chloride yields isochromen-1-one (2).

Methods: Alkaline hydrolysis of (2) gave the corresponding keto-acid (3), which is then reduced to hydroxy acid (4) then its cyclodehydration was carried out with acetic anhydride to afford 3,4- dihydroisochromen-1-one (5). Followed by demethylation step, the synthesis of target 6,8- dihydroxy-7-methyl-3-undecyl-3,4-dihydroisocoumarin (6) was achieved.

Results: In vitro antibacterial screening of all the synthesized compounds were carried out against ten bacterial strains by agar well diffusion method.

Conclusion: Newly synthesized molecules exhibited moderate antibacterial activity and maximum inhibition was observed against Bacillus subtilus and Salmonella paratyphi.

Keywords: 3, 5-Dimethoxy-4-methylhomophthalic acid, analogues of natural 3, 4-dihydroisochromen-1-one, antibacterial screening, agar well diffusion method, cyclodehydration, bacterial strains.

Graphical Abstract

[1]
Elamrani, M.; Benaissa, M. Chemical composition and antibacterial activity of the essential oil of Ononis natrix from Morocco. J. Essent. Oil. Bearing Plants, 2010, 13, 477-488.
[2]
Al-khalil, S.; Masalmeh, A.; Abdalla, S.; Tosa, H.; Iinuma, M. N-arachidylanthranilic acid, a new derivative from Ononis natrix. J. Nat. Prod., 1995, 58, 760-763.
[3]
Zhang, W.; Krohn, K.; Draeger, S.; Schulz, B. Bioactive isocoumarins isolated from the endophytic fungus Microdochium bolleyi. J. Nat. Prod., 2008, 71, 1078-1081.
[4]
Devienne, K.F.; Raddi, G.; Coelho, R.G.; Vilegas, W.J. Structure-antimicrobial activity of some natural isocoumarins and their analogues. Phytother. Phytopharm., 2005, 12, 378-381.
[5]
Di Stasi, L.C.; Camuesco, D.; Nieto, A.; Vilegas, W.; Zarzuelo, A.; Galvez, J. Intestinal anti-inflammatory activity of paepalantine, an isocoumarin isolated from the capitula of Paepalanthus bromelioides, in the trinitrobenzenesulphonic acid model of rat colitis. Planta Med., 2004, 70, 315-320.
[6]
Rama, N.H.; Saeed, A.; Bird, C.W. The synthesis of the principal dihydroisocoumarins of Ononis natrix. Liebigs Ann. Chem., 1993, 12, 1331-1333.
[7]
Krohn, K.; Flörke, U.; Rao, M.S.; Steingröver, K.; Aust, H.J.; Draeger, S.; Schulz, B. Metabolites from fungi 15. New isocoumarins from an endophytic fungus isolated from the Canadian thistle Cirsium arvense. Nat. Prod. Lett., 2001, 15, 353-361.
[8]
Saeed, A.; Mahesar, P.A. Total synthesis of achlisocoumarins I-II from Achlys triphylla. Tetrahedron, 2014, 70, 1401-1407.
[9]
Saeed, A. Isocoumarins, miraculous natural products blessed with diverse pharmacological activities. Eur. J. Med. Chem., 2016, 116, 290-317.
[10]
Saeed, A. Stereoselective synthesis of (3r)-3,4-dihydro-6,8-dimethoxy-3-undecyl-1h-[2]benzopyran-1-one and derivatives, metabolites from Ononis natrix. Helv. Chim. Acta, 2003, 86, 377-383.
[11]
Rafique, H.; Saeed, A.; Mumtaz, A. Antibacterial evaluation of some synthetic 3,4-dihydroisocoumarins. Lat. Am. J. Pharm., 2016, 35, 1545-1552.
[12]
Saeed, A.; Rafique, H.; Ashraf, Z. Synthesis and antibacterial evaluation of typharin analog: 6,8-dihydroxy-7-methyl-3-styryl-3,4-dihydroisocoumarin. J. Asian Nat. Prod. Res., 2013, 15, 130-135.
[13]
Okeke, M.I.; Iroegbu, C.U.; Eze, E.N.; Okoli, A.S.; Esimone, C.O. Evaluation of extracts of the root of Landolphia-owerrience for antibacterial activity. J. Ethno. Pharm., 2001, 78, 119-127.